Selective functionalization of crown ethers via arene chromium tricarbonyl complexes

The crown ethers dibenzo-16-crown-4 and dibenzo-18-crown-5 and a diaryl polyether were complexed by the chromium tricarbonyl group for the purpose of selective functionalization. This complexation did indeed permit exclusive functionalization of the complexed ring. CHO and CH2OH functionalities were introduced ortho to the ether group. It was noted that the nature of the two ether chains had a strong influence on the regioselectivity of the functionalization, which occurred preferentially on the side with the polyether chain. Photochemical decomplexation produced functionalized organic crown ethers.